A bet gone right
by MidnightWolf45
Summary: Winston and Eve make a wager and it somehow goes wrong for Eve; or does it. Leave comments
1. Day 1

Eve's POV

How did I get myself into this mess? Oh yeah, I remember; I was arrogant. and stupid. Now I'm wearing this school girl outfit: a white top, a red tie, and a red mini skirt. I don't know where Winston got this, but I'm wearing it; and it is very tight. Winston was already in our computer room waiting for me. How did this have to happen to me? Oh wait I remember now.

This all started this morning when I woke up late this afternoon. Last night I went out and had some drinks with some of my old college friends that were visiting town this week. I remember that we were hitting almost every bar in the the city and having the time of our lives; I even remember one of our friends getting a hangover and we had to take her back to the hotel. After our partying and shopping, I remember heading back home and waking Winston up from his slumber. I then remember forcing him to have fun with me too; I like it when ever we have fun together and I'm on top.

After getting changed into some clothes and brushing my teeth, I went downstairs and found Winston lying on the couch and watching the football game. I remember that his favorite team is playing today and I know that he didn't want to miss a single minute of that game. I decided to fix myself some brunch since it was sort of too late for breakfast and I decided to join him.

 _I see you're finally awake_

 _You could have woken me up if you didn't want me sleeping this late_

 _I did, about twenty times I tried waking you up, but you were too hungover from that night you had with your friends…..and our unexpected mating night last night._

 _I guess you're right; I would use up most of my strength if I did all of that at once. But be honest, you love it when I'm on top._

 _I do...but sometimes it can get boring._

 _What are you saying, I'm boring_

 _No!_

 _So you're saying our daily routine in bed is boring. Winston, you knew when you married me that I was no pushover kind of wolf. I wouldn't be one of those ladylike wolves who would do whatever their fathers told their daughters what to do; I even taught our daughter the same thing._

 _I know; it's why I married the most beautiful wolf in the world. But all I'm saying is you could give it a try and do a few things my way._

After hearing what he just said, I already told myself that I would never act like that. He's know me ever since we met in high school. I used to pick on him a lot back then, but after I forced him to go on a date with me to a movie theater, go to prom with me, and then have him take me to make out point we got to know each other better and truly fall in love. In fact, it was my rough and tough attitude that made me attractive to him in the first place. However, I guess when it comes to our romantic life, I have always been the one to take charge in it. Winston knows that I could never be submissive wolf, but I wonder what it would be like if I were like that. I already know, I would be a pushover. And I already know that I'm not that. I always put my paw down when it comes to something I don't trust, like, or anything I have a problem with; an example would be when my daughters Kate and Lilly started dating my new son in laws Humphrey and Garth. However, I think I'll give Winston the chance to give him that submissive wolf that he wanted.

After the game was over, I decided to have a talk with Winston about what he said. I told him that we're going to have a bet that is picked based off an arm wrestling match. We would have three matches. If he won, then I would fulfill any submissive or sexual request that he wanted to have come true for a week. However if I won, he would have to buy me that diamond necklace that I have been eyeing for weeks now. At first I thought that Winston was going to back down from this since he knew that diamond necklace I'm talking about is super expensive. However, Winston said he was all in. We started things off with the first match. Both of us were pretty strong so it took one of us a while before we could take the other down. I used all my might and took his arm down, winning the first match. The second match was the same. We would use all our might to take the other wolf down. However, some sweat got into my eyes and it distracted me long enough for Winston to slam my arm down on the table. We were now tied and ready for the final round. When we began, I used every ounce of my strength in order to win this round; also the urge to get that diamond necklace was keeping me going. I saw how my arm was pushing Winston down. I knew without a doubt that I was going to win. However, my overconfidence was my downfall when Winston turned the tables on me and slammed my arm down unexpectedly. I asked myself how this was even possible. Winston explained that he know that I always give up whenever it seems I'm close to winning any arm wrestling match or anything at all. He knew that would be his opportunity to turn the tables around and beat me.

And that's how this all happened. I lost the bet and now I'm his submissive wife for the next two weeks. The first thing I had to do was be a school girl for him and he's the professor. I don't know where he got his uniform from, but from the looks of things it must be one of Kate or Lilly's old school uniforms from high school. Now it's being used to fulfill one of Winston's dreams.

 _Hello Eve_

 _Hello professor Winston. You wanted to see me._

 _Yes! It's about your grades. You've been failing all the test that I've given and you never turn in any of the assignments that I give. Care to explain this to me._

 _I've been under a lot of stress lately; you know high school stuff._

 _I thought you were going to give me something a little more convincing so I wouldn't have to fail you. But I guess I have no choice_

 _Please Professor Winston, don't. If I fail this class, my dad is going to throw me in jail. And I mean it he will throw me in jail; he's cop. Isn't there anything I can do to get my grad up._

 _Well there is one thing you can do_

Winston would then tell me to come right here and sit on his lap. Once I sat down, I could feel his huge cock on my butt. He began to stare at my breast and started licking my neck. As he was licking me, I could feel myself shudder at the feeling of his wet tongue on my body like that. He then began to place his face inside of my breast and began licking all up inside of me. I was moaning and groaning from having him all up inside there like that. I don't know why, but it felt good. As he was doing this, he began taking off my top and began to suck on my tits. As he was sucking on them, it made my face turn completely red and I started panting. I asked: could you go a little slower professor Winston; I don't know how much more of this I can take. He said: If you want me to change that grade of your, you'll do whatever I say and not complain about it. After that he continued to suck on my tits. As this was going, I could feel myself getting wet from the experience. Winston could tell I was getting wet too. He then cleared his desk of his stuff and placed me on top of it. He began stripping me of my short skirt and then taking my panties away from me in an instant. The idea of him taking my clothes away like this made me feel embarrassed. This is a whole new territory for me since he's the top wolf and I'm not. He started things off by licking my pussy. Once his tongue was all up inside of me, my face was now completely red with pleasure and excitement. At first I thought that I wasn't really up for something like this at all since I don't have it in me to be submissive. But now, I'm really starting to enjoy this. When Winston finally finished, he placed his huge cock inside of me and started to go to town on me. He was thrusting very hard and very powerful inside of me. He would tell me that I was close to passing the class since I was so tight. As he was going, I would grab my breast just to try and hold in the pressure he was putting in me. Winston would then tell me that he was going to cum. Once he could feel it coming, he took out his cock and sprayed his juices all over my body. He then called me over to come and suck on his cock for a while. As I was sucking, he would place his paws on my forehead and made me go deeper inside of him and further so I wouldn't miss any part of his cokc and I would take it all in like a big girl. While I was doing this, Winston told me that I pass with flying colors and he was going to change my grade

Later that night, Winston was in great spirits from what we did tonight. I could tell that he loved me playing the desperate school wolf and begging to have my grade changed. However, I don't appreciate that he had to record that whole thing just so he could watch this all once the week is over.

 **Well guys, what do you think of this story. I'm hoping to continue this, but I need to hear comments from you readers. Let me know what you think of this chapter and how you think I should proceed with it. Any idea is good to me, just let me know.**


	2. Day 2

Eve's POV

I can't believe I'm doing this. I can't believe I only have 6 more days of this; 5 if you count when the day is up. Winston is making sure that he gets this whole bet for what its worth. I knew he was going to have plans for me the next morning, but I couldn't figure out what he might have planned for me.

The next morning, I got up and showered. When I got out of the shower, I realized that Winston was no where in sight. I then found a letter addressed to me. It said: "I'm waiting for you downstairs. Put what is in that box on for our little game today". I opened it and found a small device and a black maid outfit. I guess that means Winston wanted me to dress up like a maid for today. The only thing is, what does he want me to do with this device in the first place. I saw another note that said: "place the device inside of you pussy". I did what the letter said and placed that little device inside of myself. After that was taken care of, I walked downstairs to find Winston laying on the couch

 _So this is what you wanted me to wear today_

 _Yes! In case you forgot, today is your day to clean the house. However, I get to enjoy every bit of it._

 _Ok, then. I better get started_

 _Hold on! Did you put that device inside of yourself._

 _I did_

 _Good! And by the way, you have to call me Master Winston_

 _Ok, Winston_

 _Bad girl_

 _Ahhhhhhh! What was that_

 _Your punishment and my pleasure. You didn't call me master, so that was your punishment. You have to not only clean the house, but you have to do it in a sexy pose each time. If I don't like it then I will punish you. And next time, you better call me Master Winston._

 _Yes…...Master Winston_

I did what he said and started cleaning the house. The first thing I did was clean the dishes since I liked doing that first. As I was cleaning, Winston activated that device I saw him holding. He wanted me to do something. I decided that the best way to make things interesting for him was licking the dishes erotically. I would turn towards him and lick the plates and sometimes suck on the silverware.

The next thing I did was sorting our dirty clothes. Normally I would have Winston do this since I don't like doing laundry, but I had no other choice in this case. While I was sorting the clothes, he pressed the button on that device again. This time it was at its highest setting. While he had the device in my pussy, it was painful yet pleasurable at the same time. The sensation was so great that I could feel myself getting wet too. I told Winston if he could lay off, but he activated the device again. I then told Master Winston if he could turn that device down a bit; he said no.

The next thing I did was clean the bathroom. Out of all the chores that me or Winston do, I make sure that he did it. I hated the idea of cleaning it; mainly since I'm the one that makes the most mess. As I was cleaning, Winston told me to show my cleavage while I was cleaning the sink. I did what he said and began cleaning it. However, he still activated that device on me. I then noticed the skull button on the device he had. Winston said that he shouldn't be pressing it, but he wanted to see my embarrassed and red face so badly while seeing my cleavage.

After all the chores were done, Winston told me to meet him in the dining room; he was sitting on the kitchen table.

 _You did a good job Eve; you can remove that device from your pussy now_

 _Thank you Master Winston_

 _Eve, you look exhausted._

 _I am a little tired from the cleaning Master Winston._

 _I might be able to help you with that_

 _How can you do that Master Winston_

 _Come here_

 _Dah! Master Winston!_

 _Now my beautiful maid, let me help you relax_

Winston continued to squeeze my butt after I got close to him. He then began licking my neck; it made my body shiver. Then placed me on the dinner table on my back and began to take off my skirt. He then took off his pants and placed his cock inside of my pussy. He would thrust it inside of me at lighting speed. I was moaning and groaning in pleasure and pain from how he was doing this. He then had me get off the table and get on my knees and told me to start sucking on his cock. As I was sucking on it, he would thrust it in me myself to make sure that I took it all in. I wanted to have him stop so I could breath a bit, but he would not stop at all no matter what. He would say: you're a good maid for taking this all in me. I would say to him, albeit in in muffled voice: Thank you master Winston. He would then stop having me suck on him and placed me on the table again. He would then place his tongue inside of my pussy and began licking me all up inside. I was turning red in the face from all of this pleasure and ecstasy. He was making sure that he got every bit of my insides and taking in all of my incoming fluids. He then turned me over and placed his cock inside my ass. Once inside of me, he began thrusting inside of me and giving me spanking. I was taking it all in and holding it all in while he pounded me and gave me the company of his cock. He would ask me if I was feeling relaxed. I told him that it was painful at first, but I was starting to feel relaxed in my own way. After Winston finished with his thrusting and spankings, he let out all of his cum on my butt.

After that was all done, we ate dinner, watched some t.v and went to bad. For the second day of the bet, it was not too bad. I just hope the next thing he has planned is something a little less humiliating.

Winston's POV

This bet is getting good so far. I am getting my chance to take advantage of Eve and have my way with her for the next five days. Since I know I will never get this chance again, I need to make sure I use as many of my five opportunities I have left. I think I know the best way to have fun with Eve. I decided to get my two favorite pals in on this since I shouldn't be sharing it on my own. I grabbed my phone while I was asleep and sent a message to Tony and King for a game of cards tomorrow.


End file.
